Looking for love. Trace Cyrus‘ dating history has made headlines over the years as his relationships influenced his life — and his music.

Following a brief relationship with Demi Lovato, Cyrus moved on with fellow Disney Channel star Brenda Song. The couple went public with their romance in May 2010 and confirmed their engagement one year later.

“I am very excited to say, last week I asked my girlfriend Brenda Song to marry me and she said YES! We are both very excited to be engaged!” the Metro Station performer tweeted in October 2011.

Cyrus later revealed that the pair decided to press pause on their relationship. “Brenda and I have decided to go our separate ways,” he shared in a statement in June 2012. “We split up a couple of months ago. We will continue to focus on our careers. I wish Brenda the best and much success in the future. I hope everyone can respect our privacy about this situation. Thanks so much.”

The musician and the actress continued to date on-and-off for seven years before Cyrus announced that they were over for good. In February 2018, the former Ashland HIGH band member reflected on his breakup in a song named after his ex-girlfriend.

“This is not the video I intended to release today. But it seemed meant to be since I just got this video last night,” he wrote alongside the since-deleted Instagram post. “I wrote this song last year in Nashville after Brenda [and] I broke up. Her and I have both moved on and I’m extremely happy for her. She inspired me to write countless songs and was such an important part of my life. I will always cherish songs I have like this one to remind me of our crazy [seven] years together.”

The Dollface alum moved on with Macaulay Culkin and welcomed son Dakota in April 2021. Us Weekly confirmed their engagement in January 2022. Cyrus, for his part, dated Taylor Lauren Sanders from 2018 to 2020.

He later took to social media to confirm his relationship status. “Some of u might already know but I’m recently single & extremely thankful to have my family around me during this time,” he wrote via Instagram alongside a photo with his sister Miley Cyrus. “I’ve just been feeling so blessed lately! Thank u @mileycyrus for always being there. Love you sooo much sissy!”

Scroll down to relive Trace’s dating history through the years: